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      Ligand-dependent, palladium-catalyzed stereodivergent synthesis of chiral tetrahydroquinolines†

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      Chemical Science
      The Royal Society of Chemistry

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          Abstract

          The most fundamental tasks in asymmetric synthesis are the development of fully stereodivergent strategies to access the full complement of stereoisomers of products bearing multiple stereocenters. Although great progress has been made in the past few decades, developing general and practical strategies that allow selective generation of any diastereomer of a reaction product bearing multiple stereocentres through switching distinct chiral catalysts is a significant challenge. Here, attaining precise switching of the product stereochemistry, we develop a novel P-chirogenic ligand, i.e.YuePhos, which can be easily derived from inexpensive and commercially available starting materials in four chemical operations. Through switching of three chiral ligands, an unprecedented ligand-dependent diastereodivergent Pd-catalyzed asymmetric intermolecular [4 + 2] cycloaddition reaction of vinyl benzoxazinanone with α-arylidene succinimides was developed. This novel method provides an efficient route for the stereodivergent synthesis of six stereoisomers of pyrrolidines bearing up to three adjacent stereocenters (one quaternary center). Despite the anticipated challenges associated with controlling stereoselectivity in such a complex system, the products are obtained in enantiomeric excesses ranging up to 98% ee. In addition, the synthetic utilities of optically active hexahydrocarbazoles are also shown.

          Abstract

          An unprecedented ligand-dependent stereodivergent Pd-catalyzed asymmetric intermolecular [4 + 2] cycloaddition reaction of vinyl benzoxazinanone with α-aryliene succinimides was developed.

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          Author and article information

          Journal
          Chem Sci
          Chem Sci
          SC
          CSHCBM
          Chemical Science
          The Royal Society of Chemistry
          2041-6520
          2041-6539
          20 June 2022
          13 July 2022
          20 June 2022
          : 13
          : 27
          : 8131-8136
          Affiliations
          [a] College of Chemistry, Green Catalysis Center, International Phosphorus Laboratory, International Joint Research Laboratory for Functional Organophosphorus Materials of Henan Province, Zhengzhou University Zhengzhou 450001 P. R. China lierqing@ 123456zzu.edu.cn duanzheng@ 123456zzu.edu.cn
          Author information
          https://orcid.org/0000-0003-1286-6832
          https://orcid.org/0000-0002-0173-663X
          Article
          d2sc02771b
          10.1039/d2sc02771b
          9278114
          3d874d58-bd31-4a55-bff6-54929b24831a
          This journal is © The Royal Society of Chemistry
          History
          : 18 May 2022
          : 18 June 2022
          Page count
          Pages: 6
          Funding
          Funded by: National Natural Science Foundation of China, doi 10.13039/501100001809;
          Award ID: 22171245, 21702189 and 21672193
          Funded by: Zhengzhou University, doi 10.13039/501100004605;
          Award ID: JC21253007
          Funded by: Henan Provincial Science and Technology Research Project, doi 10.13039/501100017700;
          Award ID: 202102310004
          Categories
          Chemistry
          Custom metadata
          Paginated Article

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